Crystal structure of (4Z)-4-[(2E)-1-hydroxy-3-(naphthalen-2-yl)prop-2-en-1-yl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Muhammad Salim; Munawar Ali Munawar; Muhammad Nawaz Tahir; Muhammad Shahid; Khizar Iqbal Malik

doi:10.1107/S205698901500866X

. 2015 May 9;71(Pt 6):o381. doi: 10.1107/S205698901500866X

Crystal structure of (4Z)-4-[(2E)-1-hydroxy-3-(naphthalen-2-yl)prop-2-en-1-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Muhammad Salim ^a, Munawar Ali Munawar ^a, Muhammad Nawaz Tahir ^b,^*, Muhammad Shahid ^a, Khizar Iqbal Malik ^a

PMCID: PMC4459333 PMID: 26090177

Abstract

In the title compound, C₂₃H₁₈N₂O₂, the pyrazole ring subtends dihedral angles of 2.01 (13) and 1.55 (10)° with the pendant benzene ring and the naphthalene ring system, respectively. The molecule is almost planar (r.m.s. deviation for the 27 non-H atoms = 0.025 Å) and intramolecular O—H⋯O and C—H⋯O hydrogen bonds both close S(6) loops. In the crystal, very weak aromatic π–π stacking interactions between the benzene and the pyrazole rings, with centroid–centroid distances of 3.8913 (14) and 3.9285 (15) Å, are observed.

Keywords: crystal structure, pyrazole, intramolecular hydrogen bonding, π–π stacking

Related literature

For related structures, see: Chaudhry et al. (2012 ▸); Holzer et al. (1999 ▸); Malik et al. (2009 ▸). graphic file with name e-71-0o381-scheme1.jpg

Experimental

Crystal data

C₂₃H₁₈N₂O₂
M _r = 354.39
Monoclinic,
a = 6.7067 (8) Å
b = 17.525 (2) Å
c = 15.784 (2) Å
β = 101.152 (6)°
V = 1820.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.40 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T _min = 0.968, T _max = 0.986
13979 measured reflections
3574 independent reflections
1855 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.140
S = 0.99
3574 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500866X/hb7418sup1.cif

e-71-0o381-sup1.cif^{(26.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500866X/hb7418Isup2.hkl

e-71-0o381-Isup2.hkl^{(196.2KB, hkl)}

Click here for additional data file.^{(7.2KB, cml)}

Supporting information file. DOI: 10.1107/S205698901500866X/hb7418Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S205698901500866X/hb7418fig1.tif

View of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.^{(1.6MB, tif)}

. DOI: 10.1107/S205698901500866X/hb7418fig2.tif

The partial packing, showing π–π interactions.

CCDC reference: 1062997

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O2H2AO1	0.82	1.80	2.555(2)	153
C6H6O1	0.93	2.30	2.940(3)	126

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Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

S1. Comment

The crystal structures of 5-methyl-2-phenyl-4-((E)-3-phenyl-2-hydroxy- prop-2-enylidene)-1,2-dihydro-3H-pyrazol-3-one (Holzer et al., 1999), (4Z)-4-((2E)-1-hydroxy-3-(4-methoxyphenyl)prop-2-en-1- ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (Malik et al., 2009) and (4Z)-4-((2E)-1-hydroxy-3-(3-nitrophenyl)prop- 2-en-1-ylidene)-3-methyl-1-(4-methylphenyl)-1H-pyrazol-5(4H)-one (Chaudhry, et al., 2012) have been published which are related to the title compound (I, Fig. 1). (I) is synthesized for the biological studies as well as for the preparation of different metal complexes.

In (I), the benzene ring A (C1–C6) and the (4Z)-4-[(2E)-1- hydroxy-3-(naphthalen-2-yl)prop-2-en-1-ylidene]-5-methyl-2,4-dihydro-3H -pyrazol-3-one moiety B (C7 –C23/N1/N2/O1/O2) are almost planar with r.m.s. deviations of 0.0022 and 0.0179 Å, respectively. The dihedral angle between A/B is 2.30 (13)°. There exist intramolecular H-bonding of O—H···O type completing S (6) loop. There exist π–π interactions at a distance of 3.9285 (15) Å between the centroids of Cg1—Cg2ⁱ and Cg2— Cg1ⁱⁱ [i = 1 + x, y, z and ii = -1 + x, y, z], where Cg1 and Cg2 are the centroids of heterocyclic ring C (N1/N2/C7/C8/C9) and benzene ring A (Fig. 2). Similarly, there exist π–π interactions at a distance of 3.8913 (14) Å between the centroids of Cg3—Cg1ⁱ and Cg1— Cg3ⁱⁱ [i = 1 + x, y, z and ii = -1 + x, y, z], where Cg3 is the centroids of ring D (C14/C15/C16/C17/C22/C23).

S2. Experimental

4-Acetyl-3-methyl-1-phenyl-5-hydroxy pyrazole (0.218 g, 1 mmol), 2-naphthaldehyde (0.234 g, 1.5 mmol) in glacial acetic acid (10 ml) and concentrated sulfuric acid (0.2 ml) was stirred at 353–360 K for 8 h. The reaction mixture was diluted with distilled water (50 ml). The precipitate was filtered, washed with methanol and dried. The crude product was purified by column chromatography using n-hexane and ethyl acetate mixtures as eluents. The product was recrystallized form n-hexane solution to afford purple needle. Yield = 56%, m.p. = 491 K